1530-43-4

Basic information

• Product Name: BENZHYDRYL TRIPHENYLPHOSPHONIUM CHLORIDE
• Synonyms: BENZHYDRYL TRIPHENYLPHOSPHONIUM CHLORIDE;Diphenylmethyl triphenylphosphonium chloride;Benzhydryl triphenylphosphonium chloride, 98
• CAS NO: 1530-43-4
• Molecular Formula: C₃₁H₂₆P*Cl
• Molecular Weight: 464.96
• EINECS: 216-229-6
• Mol File: 1530-43-4.mol
• Article Data: 1

Chemical Properties

• Melting Point: 266-270°C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Sensitive: Hygroscopic
• BRN: 3821520
• CAS DataBase Reference: BENZHYDRYL TRIPHENYLPHOSPHONIUM CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZHYDRYL TRIPHENYLPHOSPHONIUM CHLORIDE(1530-43-4)
• EPA Substance Registry System: BENZHYDRYL TRIPHENYLPHOSPHONIUM CHLORIDE(1530-43-4)

Safety Data

• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 1530-43-4(Hazardous Substances Data)

Usage

General Description

Benzhydryl triphenylphosphonium chloride is a chemical compound that is commonly used as a phase-transfer catalyst in organic synthesis. It acts as a catalyst by facilitating the transfer of a reactant from one phase to another, typically from an aqueous phase to an organic phase. BENZHYDRYL TRIPHENYLPHOSPHONIUM CHLORIDE is a quaternary ammonium salt with a triphenylphosphonium cation and a benzhydryl anion. It is a white, crystalline solid that is soluble in organic solvents like chloroform and acetone. Benzhydryl triphenylphosphonium chloride is used in various organic reactions such as alkylation, arylation, and other types of functional group transformations. It is also used in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C31H26P.ClH/c1-6-16-26(17-7-1)31(27-18-8-2-9-19-27)32(28-20-10-3-11-21-28,29-22-12-4-13-23-29)30-24-14-5-15-25-30;/h1-25,31H;1H/q+1;/p-1

Upstream product

• 603-35-0 triphenylphosphine 
• 908093-98-1 diazodiphenylmethane 
• 7647-01-0 hydrogenchloride 
• 4214-38-4 (diphenylmethylene)triphenylphosphorane 
• 91-01-0 1,1-Diphenylmethanol 
• 1109-01-9 diphenyldiazomethane triphenylphosphazine 

Downstream Products

• 4471-17-4 diphenylmethyl radical 

Relevant articles and documents

Ion-pairing of phosphonium salts in solution: C-H...halogen and C-H...π hydrogen bonds

The 1HNMR chemical shifts of the C(α)-H protons of arylmethyl triphenylphosphonium ions in CD2Cl2 solution strongly depend on the counteranions X-. The values for the benzhydryl derivatives Ph2CH-PPh3+ X -, for example, range from δH=8.25 (X -=Cl-) over 6.23 (X-=BF4 -) to 5.72ppm (X-=BPh4-). Similar, albeit weaker, counterion-induced shifts are observed for the ortho-protons of all aryl groups. Concentration-dependent NMR studies show that the large shifts result from the deshielding of the protons by the anions, which decreases in the order Cl- > Br- a‰ BF4 - > SbF6-. For the less bulky derivatives PhCH2-PPh3+ X-, we also find C-H...Ph interactions between C(α)-H and a phenyl group of the BPh4- anion, which result in upfield NMR chemical shifts of the C(α)-H protons. These interactions could also be observed in crystals of (p-CF3-C6H4)CH2-PPh 3+ BPh4-. However, the dominant effects causing the counterion-induced shifts in the NMR spectra are the C-H...X- hydrogen bonds between the phosphonium ion and anions, in particular Cl- or Br-. This observation contradicts earlier interpretations which assigned these shifts predominantly to the ring current of the BPh4- anions. The concentration dependence of the 1HNMR chemical shifts allowed us to determine the dissociation constants of the phosphonium salts in CD2Cl2 solution. The cation-anion interactions increase with the acidity of the C(α)-H protons and the basicity of the anion. The existence of C-H...X- hydrogen bonds between the cations and anions is confirmed by quantum chemical calculations of the ion pair structures, as well as by X-ray analyses of the crystals. The IR spectra of the Cl- and Br- salts in CD2Cl2 solution show strong red-shifts of the C-H stretch bands. The C-H stretch bands of the tetrafluoroborate salt PhCH 2-PPh3+ BF4- in CD 2Cl2, however, show a blue-shift compared to the corresponding BPh4- salt.